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Posted: Wednesday November 18, 2009 11:57AM; Updated: Wednesday November 18, 2009 12:04PM
Jon Heyman

Roy Halladay sweepstakes could be just another Yankees-Red Sox bout

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Roy Halladay
Roy Halladay is 18-6 with a 2.84 ERA in 37 career games against the Yankees.
Mark Goldman/Icon SMI

The Yankees recently called the Blue Jays to express interest in superstar pitcher Roy Halladay. And while the Yankees made the very same call last summer with no hope of acquiring Halladay, this time they have a real reason to believe they may actually have a legitimate chance to make a blockbuster trade.

If that's a positive development for the World Series champs, the twist is that they might be battling the rival Red Sox for the star pitcher who's well-known as a Yankee killer, as his 18-6 record against the Bronx Bombers attests.

Here is the most obvious reason the Yankees (or Red Sox) may now finally have a legit shot to trade for arguably baseball's best pitcher: New Toronto GM Alex Anthopoulos is making it clear he is genuinely willing to consider a deal with either the Yankees or Red Sox, a sharp contrast to Anthopoulos' predecessor, J.P. Ricciardi, who had GMs convinced he'd never make a Halladay trade with either the Yankees or Red Sox.

Speaking generally about the concept of intra-division trades, Anthopoulos said by phone Tuesday, "This isn't the NBA where you're talking about one of five guys on the floor at all times ... If you have two trades that are identical, and one is in the division and one is outside, then it's easy to go outside the division. However, if the trade is better inside the division, I think you have to take a look at it. We have to do what's best for our organization."

Other GMs said they believe Anthopoulos also understands the Jays aren't ready to overtake the Yankees or Red Sox yet and has the full faith of upper management, who appeared ready to fire Ricciardi even before he botched the Halladay trade talks by not finding a suitable trade partner when his value was highest. Of course, the possibility also remains that the Jays could still hold Halladay until the summer, when his value would still be close to what it is now.

Last summer the Yankees never felt the urgency to make an offer for Halladay because they never felt Ricciardi would trade him to Boston. Back in July, Toronto was also asking for both Joba Chamberlain and Phil Hughes in a bigger package, and the Yankees never were going to do that. But with a year gone by now, the World Series winners might have a reasonable expectation that either Chamberlain or Hughes in a package might at least get the ball rolling. The Yankees also have several catching prospects to entice the Blue Jays, including Jesus Montero, who is still only 19 but is said by one scout to be "off the charts" as a hitting prospect and "better than he's given credit for as a catcher." (The Red Sox also have several excellent prospects, and probably made the best offer for Halladay last summer, despite no reasonable expectation it might be accepted.)

And here's yet another potential reason the Yankees (or Red Sox) might have an edge this time around: While Halladay's latest desires are not yet known (and agent Greg Landry did not return calls), with a year to go before free agency a player in Halladay's position can leverage his no-trade clause to engineer a trade to a team amenable to an extension. The Yankees have not heard that this will be the case. But if that happens here, the field could be limited to the teams who can pay a franchise pitcher. This is often the case when talking about big stars, and it was two years ago when Johan Santana was being shopped by the Twins -- the field was quickly winnowed to the two New York teams plus Boston, the three teams that could most easily work Santana into their budgets.

Halladay gave the Jays a lot of latitude last summer, as sources indicate he provided a nice-sized list of preferred teams with no stings attached. The preferred list was believed to include both the Yankees and Red Sox, as Halladay is thought to prefer staying in the East, training in Florida (he lives in Dunedin, Fla.) and -- most of all -- playing for a winner, which is another reason the Yankees and Red Sox could have the inside track here. The Phillies, who looked hard last summer at Halladay before turning to Cliff Lee, are obviously another team that fit all three of those requirements.

Anthopoulos indicated via phone that the Jays generally prefer trades that are "clean" and "seamless," meaning they'd prefer to do a deal without giving prospective acquiring teams a window to negotiate an extension with traded players. But he didn't say whether he'd rule out a negotiating window, as Ricciardi did before him, and Anthopoulos sure isn't using Ricciardi as any sort of guideline. If anything, he's doing the opposite.

If windows are allowed this time, that would seem to favor the big-market teams' chances to land Halladay. As one GM said, "(Halladay) could use his no-trade clause as a way to get a Santana or (CC) Sabathia deal," meaning $23 million a year. If Halladay does do that, he'd effectively limit the field to a precious few, including the Yankees and Red Sox.

With or without an extension, Halladay's trade value has been seriously diminished since last summer as his current deal would provide an acquiring team with only one year at a reasonable rate ($16 mil per), rather than one-plus (and two postseasons), before any possible expensive extension. With all the new variables, here are the possibilities for Halladay ...

1. Yankees: Even with Andy Pettitte more likely than not to return, pitching will be their focus. Halladay would make them a prohibitive favorite to repeat.

1A. Red Sox: One agent said the Red Sox seem even more motivated than ever. And they probably made the best offer for Halladay last summer (Clay Buchholz, Justin Masterson, Michael Bowden, Nick Hagadone and a positional prospect), though they won't repeat that bid now, even with the Yankees competing for Halladay. (Technically they can't, as Masterson and Hagadone went to Cleveland for Victor Martinez.)

2. Blue Jays: Team president Paul Beeston, who elevated himself to permanent status, is said to be such an admirer of Halladay that he have never wanted to trade him. Several GMs believe Beeston will want to keep Halladay, at least until the summer. And one GM said, "His value will be the same this summer."

3. Phillies: They are a win-now team, and while GM Ruben Amaro said last week that the focus is on third base and the bullpen, they are saving more than you'd think with the expiring contracts of Adam Eaton, Geoff Jenkins and Brett Myers. They also have the prospects to do it.

4. Angels: There's no evidence they're in the mix and are probably slightly more likely to take back John Lackey, but they are known as a stealth mover.

5. Mets: They've said they'll look into. But eventually, the likelihood is that they won't want to dedicate $46 million to two pitchers when they have other holes to fill (left field, catcher, bullpen, possibly second base).

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